Test this crude product for the presence of unreacted salicylic acid using the ferric chloride test. Add 5 mL (0.05 mole) of acetic anhydride, followed by 5 drops of conc. Adopted a LibreTexts for your class? 5. If you have difficulty, look at the banana oil experiment. Only the salicylate ion complexes to iron(III). In this experiment, phosphoric acid will be used as the catalyst. Rinse the crystals several times with small portions (5 mL) of cold water and air dry the crystals on a Buchner funnel by suction until the crystals appear to be free of solvent. According to the data in the Merck Index, if 1.0 g of aspirin is dissolved in 100 mL of water at 37 °C , how much aspirin will precipitate out of solution when it is cooled to 25. Description:This project is about synthesizing green aspirin by replacing sulfuric acid with a natural acid in the synthesis of aspirin. Weigh out 3.0 g of salicylic acid and place in a 250 ml Erlenmeyer flask. One of the oldest drugs! The percent yield of the crude product will be determined for this reaction. A round bottom flask was charged with 1 g (0.0072 mol) of salicylic acid, 3 ml (0.03 mol) of acetic anhydride and 4 drops of 85% phosphoric acid as catalyst. One popular drug that does both is aspirin. If crystals do not appear, you can scratch the walls of the flask with a stirring rod to induce crystallization. 6. Academia.edu is a platform for academics to share research papers. But still a very large part of the world’s population has inadequate or no access to such essential and life-saving medicines like acetyl-salicylic acid. First, gather the chemicals and equipment used to synthesize the aspirin. 3.0 g salicylic acid; 6 mL acetic anhydride* 5-8 drops of 85% phosphoric acid or concentrated sulfuric acid* Distilled water (about 50 mL) 10 … The product will be analyzed by three different methods: melting point, titration, and spectroscopic assay. 2. Synthesis of Aspirin Salicylic acid derivatives, or salicin, are found in the bark of the willow tree. The aspirin isolated in this step is the “crude product”. During this semester, you will have an opportunity to isolate some pharmacologically active natural products and to synthesize other active compounds from suitable starting materials. Also, your melting point range may be greater than 2 degrees. [ "article:topic", "Aspirin", "showtoc:no" ], https://chem.libretexts.org/@app/auth/3/login?returnto=https%3A%2F%2Fchem.libretexts.org%2FBookshelves%2FAncillary_Materials%2FLaboratory_Experiments%2FWet_Lab_Experiments%2FOrganic_Chemistry_Labs%2FExperiments%2F1%253A__Synthesis_of_Aspirin_(Experiment), 2: Synthesis of Acetaminophen (Experiment), SYNTHESIS OF ASPIRIN (acetylsalicylic acid), information contact us at email@example.com, status page at https://status.libretexts.org. Analgesic (painkiller)! Measure out 6.0 ml of acetic anhydride and add this to your flask. Determination Of The Contents Of Cold Drinks. Normally, you measure reactants to at least two significant figures. The synthesis of aspirin may be achieved in one simple step, O-acetylation of salicylic acid (Figure 1), which is incorporated into many undergraduate synthetic chemistry laboratory courses. H 2 SO 4 (use a dropper, H2SO4 is highly corrosive) and swirl the flask gently until the salicylic acid dissolves. Determine the moles of aspirin from the titration and calculate the percent purity of the crude aspirin product from the titration analysis. The product will appear as a solid mass when crystallization is completed. When the aspirin was prepared, it was isolated and filtered. In folk medicine, willow bark teas were used as headache remedies and other tonics. Dissolve the final product in a minimum amount (no more than 2-3 mL) of. Excess chemicals must be disposed of in the plastic tub of water. If you spill a lot of either of these, notify your instructor. Abstract and Figures This aim of this experiment focuses on the synthesis of pure aspirin (acetylsalicylic acid) from ethanoic anhydride and salicylic acid … IUPAC NAME: 2-acetoxybenzoic acid 9. In this experiment, the crude product will be the desired product. The experiment conducted in this report will synthesize, purify and determine the percentage yield of aspirin. The melting point range of pure aspirin is 138-140 C and the melting point range of the salicylic acid starting material is 158-161 C. The product then is purified by repeated process called crystallization. The aspirin product is not very soluble in water so the aspirin product will precipitate when water is added. Clearly state if the samples are below the maximum allowable limit for percent salicylic acid (0.15 %). 3. This is your percent yield. You can do this at your bench. In this case, one molecule (salicylic acid) provides both the "alcohol" and the carboxylic acid. The purity of the product will also be analyzed. Unless otherwise noted, LibreTexts content is licensed by CC BY-NC-SA 3.0. Allow the air to be drawn through the solid and filter paper for 15 minutes. Cool the mixture slightly in an ice bath until crystallization is completed. When the product is completely dry, weigh the product, determine its melting point (lit mp 135-136 °C) and calculate the percentage yield. This experiment uses salicylic acid, acetic anhydride and phosphoric acid. After synthesis and analysis, it will be deter-mined if the crude and recrystallized samples were composed solely of either salicylic acid, acetylsalicylic acid, or a combination of both (3). Don't let the acetic anhydride contact your skin and don't get the vapors in your eyes. Why is it not necessary to measure the volume of acetic anhydride to two significant figures? Add 10 drops of aqueous 1% ferric chloride solution to a test tube containing a few crystals of the compound to be tested dissolved in 5 mL water and note the color. The percentage yield of the synthesis was calculated to be 78.42%. Click here to let us know! In this experiment aspirin was synthesized from salicylic acid and acetic anhydride. Next add 20 ml of distilled water and cool in an ice bath. What is the theoretical yield of aspirin (in two significant figures). It is the acetyl derivative of salicylic acid and is an example of a salicylate drug. When the product is completely dry, weigh its weight, determine its melting point (lit mp 135 °C) and calculate the percentage yield of this recrystallized product. Add 50 mL of water and cool the mixture in an ice bath. A small amount of a strong acid is used as a catalyst which speeds up the reaction. An experiment is described that is suitable for the early portion of the laboratory in a general chemistry course and integrates organic examples. For more information contact us at firstname.lastname@example.org or check out our status page at https://status.libretexts.org. Figure 1: Synthesis of aspirin (Clayden, et al., 558). This reaction is the reverse of the synthesis reaction. A spectrometer (Spectronic 20), salicylic acid, iron (III) nitrate, iron (III) chloride, phosphoric acid, sulfuric acid, acetic anhydride, anhydrous sodium acetate, methyline chloride, hydrochloric acid, and samples of old, expired aspirin in order to synthesize aspirin in four … The synthesis reaction of aspirin is shown below: Since acetic acid is very soluble in water, it is easily separated from the aspirin product. H. Heat the flask gently on the steam bath for at least 10 minutes. Introduction: Charles Frederic Gerhardt, a French chemist was the first to prepare aspirin in 1853. Wash the beaker and the funnel with 5 to 10 mL of water. The temperature of an alcohol thermometer was equilibrated in a beaker of room temperature tap water. The liquid is mostly water and can be washed down the sink. Filter the solution through a Buchner funnel to remove any insoluble impurities or polymers that may have been formed. If you spill some, wipe it up with a wet paper towel and throw the towel in the trash. Activity 1: Synthesis of Aspirin. Plot a Beer’s Law graph of the standard 0.15% salicylic acid solution (C) on excel with Absorbance (yaxis) vs % salicylic acid (x-axis). CONTINUED… 1) Substitution on carboxyl groups may affect the potency and toxicity. ment (synthesis of aspirin masses, theoretical yield, percent yield and error, and TLC analysis). The synthesis involved the reaction of salicylic acid and acetic anhydride in the presence of a catalyst, phosphoric acid, H3PO4. A “purified product” can be obtained through recrystallization of the crude product in hot ethanol. Add 5 mL (0.05 mole) of acetic anhydride, followed by 5 drops of conc. 7. It is the two-step synthesis of aspirin starting from oil of wintergreen. Calculate the weight of your product by subtracting the weight of the paper and bag from the total. What percent of this did you get? Stir the crude solid with 25 mL of a saturated aqueous sodium bicarbonate solution in a 150 mL beaker until all signs of reaction have ceased (evolution of \(CO_2\) ceases). Do this test with 1.phenol, 2. salicylic acid, and 3. your crude product. Carefully add 5 to 10 drops of 85% phosphoric acid, a catalyst, to the flask and swirl to mix everything thoroughly. In this experiment, the researchers combined the salicylic acid, glacial acetic acid and phosphoric acid … Submit the crystalline sample in a small vial with proper labeling to your instructor. Wash the crystals with 2-3 ml of chilled water. The acetic anhydride and phosphoric acid can cause bad burns. Nowadays, salicylic acid is administered in the form of aspirin which is less irritating to the stomach than salicylic acid. Collect the product by vacuum filtration and rinse out of the flask with a few milliliters of cold petroleum ether. Record the weight of the crude solid which probably contains water. Aspirin is also known as acetylsalicylic acid. Do not add the water until crystal formation is complete. It was equipped with a reflux condenser, heated to 100 F and stirred vigorously. Put the dry aspirin and the filter paper into a pre-weighed plastic bag and weigh again. The purity of the product as a pharmaceutical is crucial, and 11. Acetyl-salicylic acid is on the WHO Model List of Essential Medicines, the most important medications needed in a basic health system. Download CBSE XII Chemistry Project : PREPARATION OF ASPIRIN AND ACETAMINOPHEN. Synthesis of Aspirin Synthesis Purification Characterization. The salicylic acid and aspirin may cause irritation to your skin or eyes, but are basically not hazardous. Be sure to do this in the hood and wear your goggles. Major Chemical Concept. If acetylsalicylic acid does not begin to crystallize out, scratch the walls of the flask with a glass rod. The synthesis of aspirin is known in organic chemistry as an esterification reaction. In the 5th century B.C., Hippocrates ground the bark into a powder, and later, the Natives Americans chewed on the bark to alleviate fever and pain1. Write a structure for the ester formed from acetic acid and ethanol. Synthesis of Aspirin 1618 Words | 7 Pages. To add titles to the plot, select layout, axis titles, and then chart titles. Determination Of Caffeine In Tea Samples. Medicine Analysis – Synthesising Aspirin results After recrystallisation differences between the crude and purified aspirin were noted. The purity of the product formed will then be determined by a series of tests. Synthesis of Aspirin By: Jon Torre Purpose: To determine which of four catalysts yields the fastest reaction rate in the acetylation of salicylic acid (1) to form acetylsalicylic acid (2). Analgesics are compounds used to reduce pain, antipyretics are compounds used to reduce fever. Patented by Bayer in 1893! Louis; Chemistry). 8. 2) Reducing the acidity of the –COOH, retains the analgesic action of salicylic acid , but it is devoid of the anti- inflammatory properties. In lower doses, aspirin … Citric acid and pineapple juice were used as possible green catalysts but only citric acid worked when used in a high concentration. Reactions: Procedure and Results: Aspirin Synthesis Tap water was heated on a steam bath in a 250 mL beaker. Aspirin is an ester that has high molecular weight and it not soluble in water hence the solid can be separated by crystallization process. This is a substitution reaction in which an alcohol (the –OH group in salicylic acid) reacts with acetic anhydride to form an ester, aspirin. Cool the solution to room temperature and then in a ice-bath. NSF CCLI Project Page 1 EXPERIMENT Aspirin: Synthesis and NMR Analysis Introduction: When salicylic acid reacts with acetic anhydride in the presence of an acid catalyst, acetylsalicylic acid, or aspirin, is produced according to the following equation. Aspirin became commercially available in 1899 and today it is estimated that over a trillion aspirin tablets have been consumed by those in need of its curative effects. One of the most consumed drugs (Production in the US is 10 million Kg/year) Aspirin: Biological activity! Formation of an iron-phenol complex with Fe(lll) gives a definite color ranging from red to violet, depending upon the particular phenol present. One of the choicest Chemistry projects for class 12 studnets is the making of Aspirin which a common name for a compound named acetylsalicylic acid, majorly used as a pain killer in our day to day use. • For a subset of the people, aspirin may help prevent heart attacks and strokes. This laboratory project involves the synthesis, characterization, and study of some reactions of acetylsalicylic acid, and the comparison of acetylsalicylic acid with the major components of various commercial brands of aspirin tablets. These natural products have been obtained from plants, minerals, and animals. It is the two-step synthesis of aspirin starting from oil of wintergreen. The % concentration for samples A and B can be determined by plugging in the absorbance readings for those samples into the linear equation and solving for x. Over history, many compounds obtained from nature have been used to cure ills or to produce an effect in humans. Aspirin is used in the treatment of migraine • Aspirin is an important part of treatment of those who have had a myocardial infraction (heart attack). Have questions or comments? Be sure to wear gloves and safety goggles when using these chemicals. The mechanism for this synthesis provides examples of three major classes of chemical reactions: hydrolysis, condensation, and proton transfer. The theoretical (maximum) yield is 3.9 grams. The aspirin isolated in this step is the “crude product”. The synthesis of aspirin is how You make it in a chemical lab or a chemical plant. 8. Synthesis of Aspirin. Aim The aim of this project was to synthesise aspirin using two methods of heating and to compare the percentage yield and melting points of the product synthesised by the two methods. To determine the amount of aspirin in the whole of the given solution. Salicylic acid, through acetylation, gives acetylsalicylic acid, known as Aspirin… Filter the solid aspirin through a piece of pre-weighed filter paper using a Buchner funnel and the aspirator. University of Missouri–St. A “purified product” can be obtained through recrystallization of the crude product in hot ethanol. The experimental melting point range of aspirin was determined to be 122 -132°C. until dry. Vacuum filter the product using a Buchner funnel. Record it in your notebook and turn in your product to the Stockroom. Place 2.0 g (0.015 mole) of salicylic acid in a 125-mL Erlenmeyer flask. Right click a data point and select add trend line. 1. In this experiment you will synthesize aspirin and determine the yield or fraction of the theoretical amount which can be made. The impure (crude) aspirin was powered and fluffy with small clumps and was slightly yellow in colour whereas the pure aspirin has … The excess acetic acid will be quenched with the addition of water. 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